Water → HCID 13939012, compound

HRID 330497Notes

Reaction equation

HRID 330497 reaction equation
[H-].[Na+].[CH2:3]([O:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[C:21]2[OH:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[I-].[Na+].[OH2:29]>CN(C)C=O.O1CCCC1>[CH2:3]([O:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[C:21]2[O:26][CH2:17][CH:16]([OH:15])[CH2:25][OH:29])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 139390085-(Dodecyloxy)naphthalen-1-ol

Product 1

HCID 13939012HCID 13939012, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2.19 g of 50% sodium hydride in 80 ml of dimethylformamide, under argon, was added with stirring a solution of 12 g of 5-(dodecyloxy)-1-naphthalenol in 60 ml of tetrahydrofuran over 1/2 hour. A 2 g portion of sodium iodide and 9.77 g of solketal mesylate were added and the mixture was stirred overnight. The mixture was diluted with water and extracted with ether. The ether extract was washed with dilute sodium hydroxide, then brine, dried, filtered through silica gel and the solvent removed. The residue was refluxed in a mixture of 100 ml of methanol, 16 ml of water and 1 ml of concentrated sulfuric acid for one hour, then cooled and the solid collected. This solid was dissolved in boiling chloroform containing magnesium sulfate and activated carbon and filtered through diatomaceous earth. The filtrate was evaporated and the residue recyrstallized from carbon tetrachloride, giving 8 g of the desired compound as an off-white solid, mp 143°-144° C.

Workup

  1. additionunder argon, was added
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with dilute sodium hydroxide
  5. dry with materialbrine, dried
  6. filtrationfiltered through silica gel
  7. customthe solvent removed
  8. temperatureThe residue was refluxed in a mixture of 100 ml of methanol, 16 ml of water and 1 ml of concentrated sulfuric acid for one hour
  9. temperaturecooled
  10. customthe solid collected
  11. dissolutionThis solid was dissolved
  12. additioncontaining magnesium sulfate and activated carbon
  13. filtrationfiltered through diatomaceous earth
  14. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-74991403dec04afa84e2b1875d2564eb
Source dataset
uspto-grants-1990_01
Patent number
US04897385

Reaction notes

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